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  • 1.
    Bernlind, Christian
    Stockholm University, Faculty of Science.
    Synthesis of LPS epitopes containing Kdo, L-, and D-Glycero-D-manno-heptose to be used in potential conjugate vaccines against Haemophilus species1998Doctoral thesis, comprehensive summary (Other academic)
  • 2.
    Ruda, Katinka
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of inositol phosphoglycans and analogues thereof1998Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis describes the synthesis of inositol phosphoglycans (IPG) corresponding to glycosyl-phosphatidylinositol (GPI) anchors found on the cell surface of the parasite Leishmania. Synthesis of an IPG which is a putative second messenger for insulin, and of analogues thereof is also discussed.

    The IPG structures synthesized contain mono-, tri-, and hexasaccharides linked to an inositol phosphate. Analogues of the putative second messenger contain glucosamine, instead of myo-inositol phosphate, coupled to either phosphorylated D-mannose or phosphorylated L-fucose. The synthetic work involved the development of procedures for obtaining optically pure myo-inositol-glucosamine derivatives, the formation of phosphomono- and diesters (both cyclic and acyclic) and oligosaccharide synthesis.

  • 3.
    Rundlöf, Torgny
    Stockholm University.
    NMR studies of Carbohydrate Structure and Dynamics in Solution1998Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Methods for studies of the structures of carbohydrates in solution and their dynamics are presented. Approaches employing nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), force-field computer simulations and chemical methods are described.

    First, methods for determinations of the structures of natural carbohydrates are described, exemplified by the galactofuranoside and glycerol residues and the phosphodiester moiety found in the O-antigenic polysaccharide from Escherichia coli O28. These structures are determined by the use of NMR spectroscopy, MS and chemical degradations/derivatizations.

    Subsequently, approaches for determination of the three-dimensional structures and dynamics of oligosaccharides in solution are presented. Carbon-13 NMR spin relaxation times and nuclear Overhauser effects (NOEs) were measured for the pentasaccharide lacto-N-fucopentaose-1 and for a vicinally disubstituted trisaccharide. Carbon relaxation data were used to describe the dynamics in terms of overall and internal correlation times and generalized order parameters according to the model-free approach. In addition, three-bond proton-carbon coupling constants, proton NOEs and transverse rotating-frame Overhauser effects (TROEs) across the glycosidic linkages were measured for the trisaccharide. The proton NOEs and TROEs were used to calculate proton-proton distances within and between the different sugar residues.

    Langevin dynamics and Metropolis Monte Carlo simulations were performed for the trisaccharide. Averaged proton-proton distances obtained from the simulations were compared to distances obtained from the NOE and TROE measurements. Three-bond proton-carbon coupling constants were calculated from the simulations and compared to the couplings determined by NMR. The comparisons of interglycosidic distances and coupling constants in many cases reveal poor agreement.

    A recent method for studies of biomolecular three-dimensional structure in solution was employed to the tetrasaccharide lacto-N-neotetraose (LNnT). It was dissolved in an aqueous dilute liquid crystalline medium and residual dipolar couplings were measured. The orientations of the interatomic vectors in the molecule were obtained from a structure generated by molecular modeling. The measured couplings showed good agreement with couplings calculated from the orientations of the vectors in the three-dimensional structure of LNnT.

  • 4.
    Öhberg, Liselotte
    Stockholm University.
    Synthesis of a key derivative of glycosylphosphatidylinositol substances and synthesis of spacer glycosides for use in the formation of glycoconjugates and of self-assembled monolayer surfaces1998Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The first chapter of this thesis describes glycosylation strategies for obtaining derivatives of 2-amino-2-deoxy-a-D-glucopyranosyl-(1-->6)-D-myo-inositol, a key building block for synthesis of glycosylphosphatidylinositol anchor substances and also proposed to be part of a second messenger for insulin.

    The second chapter describes the synthesis of bifunctional oligoethylene glycol spacers and glycosylation of these for use in formation of glycoconjugates. Synthesis of glycosyl succinimides and their conversion into glycoconjugates are also described.

    In the third chapter, synthesis of various terminated alkane thiols are described for use in formation of self-assembled monolayer surfaces. Globotriose linked alkane thiols with or without oligoethylene glycol spacers in between were mixed with hydroxyl or oligoethylene glycol terminated alkane thiols for formation of model surfaces.

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